CH467744A - Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen - Google Patents
Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenenInfo
- Publication number
- CH467744A CH467744A CH1531868A CH1531868A CH467744A CH 467744 A CH467744 A CH 467744A CH 1531868 A CH1531868 A CH 1531868A CH 1531868 A CH1531868 A CH 1531868A CH 467744 A CH467744 A CH 467744A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- carbon atoms
- formula
- alkyl
- dibenzo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920001774 Perfluoroether Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 3
- CTWZJMQDNRRAAP-UHFFFAOYSA-N 3-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)propan-1-amine Chemical compound C1=CC2=CC=CC=C2C(=CCCN)C2=CC=CC=C21 CTWZJMQDNRRAAP-UHFFFAOYSA-N 0.000 description 2
- -1 5- (3-butylideneaminopropylidene) -5H-dibenzo- (a, d) cycloheptene Chemical compound 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings
- C07C211/32—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings containing dibenzocycloheptane or dibenzocycloheptene ring systems or condensed derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Display Racks (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12083561A | 1961-05-24 | 1961-05-24 | |
| US14022361A | 1961-09-25 | 1961-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH467744A true CH467744A (de) | 1969-01-31 |
Family
ID=26818813
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1531868A CH467744A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen |
| CH628562A CH464893A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1532268A CH467743A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1532168A CH465599A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1531968A CH467238A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen |
| CH1532068A CH464903A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1104067A CH464900A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH628562A CH464893A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1532268A CH467743A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1532168A CH465599A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1531968A CH467238A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen |
| CH1532068A CH464903A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
| CH1104067A CH464900A (de) | 1961-05-24 | 1962-05-24 | Verfahren zur Herstellung von Dibenzocycloheptenen |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE617967A (da) |
| BR (1) | BR6239240D0 (da) |
| CH (7) | CH467744A (da) |
| CY (1) | CY354A (da) |
| DE (2) | DE1593098A1 (da) |
| DK (6) | DK106326C (da) |
| FI (3) | FI41391B (da) |
| FR (1) | FR2516M (da) |
| GB (1) | GB1008263A (da) |
| GT (1) | GT197016875A (da) |
| MY (1) | MY6700003A (da) |
| NO (1) | NO121833B (da) |
| SE (8) | SE325269B (da) |
-
1962
- 1962-05-16 GB GB18913/62A patent/GB1008263A/en not_active Expired
- 1962-05-18 FI FI1007/62A patent/FI41391B/fi active
- 1962-05-21 DE DE19621593098 patent/DE1593098A1/de active Pending
- 1962-05-21 DE DE19621468212 patent/DE1468212A1/de active Pending
- 1962-05-22 BR BR139240/62A patent/BR6239240D0/pt unknown
- 1962-05-22 BE BE617967A patent/BE617967A/fr unknown
- 1962-05-23 DK DK166663AA patent/DK106326C/da active
- 1962-05-23 DK DK106264AA patent/DK106278C/da active
- 1962-05-23 DK DK106064AA patent/DK108151C/da active
- 1962-05-23 DK DK106164AA patent/DK107420C/da active
- 1962-05-23 NO NO144482A patent/NO121833B/no unknown
- 1962-05-23 DK DK232162AA patent/DK110035C/da active
- 1962-05-24 SE SE13207/65A patent/SE325269B/xx unknown
- 1962-05-24 CH CH1531868A patent/CH467744A/de unknown
- 1962-05-24 SE SE5885/62A patent/SE317369B/xx unknown
- 1962-05-24 CH CH628562A patent/CH464893A/de unknown
- 1962-05-24 CH CH1532268A patent/CH467743A/de unknown
- 1962-05-24 CH CH1532168A patent/CH465599A/de unknown
- 1962-05-24 CH CH1531968A patent/CH467238A/de unknown
- 1962-05-24 CH CH1532068A patent/CH464903A/de unknown
- 1962-05-24 CH CH1104067A patent/CH464900A/de unknown
- 1962-08-22 FR FR907533A patent/FR2516M/fr not_active Expired
-
1964
- 1964-02-27 DK DK97064AA patent/DK111679B/da unknown
-
1965
- 1965-05-14 SE SE635365A patent/SE318869B/xx unknown
- 1965-10-12 SE SE13209/65A patent/SE326441B/xx unknown
- 1965-10-12 SE SE13204/65A patent/SE323364B/xx unknown
- 1965-10-12 SE SE13210/65A patent/SE325874B/xx unknown
- 1965-10-12 SE SE13211/65A patent/SE326442B/xx unknown
- 1965-10-12 SE SE13205/65A patent/SE326440B/xx unknown
-
1966
- 1966-10-03 FI FI2588/66A patent/FI41647B/fi active
- 1966-10-03 FI FI2587/66A patent/FI41646B/fi active
- 1966-10-14 CY CY35466A patent/CY354A/xx unknown
-
1967
- 1967-12-31 MY MY19673A patent/MY6700003A/xx unknown
-
1970
- 1970-05-11 GT GT197016875A patent/GT197016875A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO121833B (da) | 1971-04-19 |
| MY6700003A (en) | 1967-12-31 |
| DK110035C (da) | 1968-09-02 |
| FR2516M (fr) | 1964-05-11 |
| SE317369B (da) | 1969-11-17 |
| GT197016875A (es) | 1971-11-02 |
| SE325874B (da) | 1970-07-13 |
| CH467238A (de) | 1969-01-15 |
| DK107420C (da) | 1967-05-29 |
| DE1468212A1 (de) | 1969-01-02 |
| SE326442B (da) | 1970-07-27 |
| FI41646B (da) | 1969-09-30 |
| CH465599A (de) | 1968-11-30 |
| DK108151C (da) | 1967-09-25 |
| GB1008263A (en) | 1965-10-27 |
| DK111679B (da) | 1968-09-30 |
| CH467743A (de) | 1969-01-31 |
| SE325269B (da) | 1970-06-29 |
| BE617967A (fr) | 1962-11-22 |
| SE326440B (da) | 1970-07-27 |
| CH464893A (de) | 1968-11-15 |
| SE326441B (da) | 1970-07-27 |
| CH464903A (de) | 1968-11-15 |
| CH464900A (de) | 1968-11-15 |
| FI41391B (da) | 1969-07-31 |
| DK106278C (da) | 1967-01-16 |
| FI41647B (da) | 1969-09-30 |
| DE1593098A1 (de) | 1969-10-16 |
| CY354A (en) | 1966-10-14 |
| SE323364B (da) | 1970-05-04 |
| SE318869B (da) | 1969-12-22 |
| DK106326C (da) | 1967-01-23 |
| BR6239240D0 (pt) | 1973-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH494730A (de) | Verfahren zur Herstellung von Dibenzocyclopentenen | |
| CH450397A (de) | Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-10,11-dihydrocycloheptenen | |
| EP0043507B1 (de) | 2,4-Dioxa-7,10-methano-spiro(5,5)undecane, deren Herstellung sowie diese enthaltende Riechstoffkompositionen | |
| EP0025869A1 (de) | 3-Methyl-cyclohexadecen-5-on-1, Verfahren zu seiner Herstellung und seine Verwendung als Riechstoff | |
| EP0004052B1 (de) | 13-Oxabicyclo(10.3.0)pentadecan, dessen Herstellung und Verwendung als Riechstoff, sowie dieses enthaltende Riechstoffkompositionen | |
| CH467743A (de) | Verfahren zur Herstellung von Dibenzocycloheptenen | |
| CH411847A (de) | Verfahren zur Herstellung von Kampferderivaten | |
| AT281823B (de) | Verfahren zur Herstellung neuer Zimtsäureamide | |
| DE1046063B (de) | Verfahren zur Herstellung neuer, amoebicid wirkender Acetanilide | |
| AT283363B (de) | Verfahren zur Herstellung neuer Zimtsäureamide | |
| AT254166B (de) | Verfahren zur Herstellung von neuen 5-(3'-sek.Aminopropyl)-5H-dibenzo[a,d]cycloheptenen bzw. den 10,11-Dihydroderivaten derselben | |
| AT162899B (de) | Verfahren zur Darstellung von neuen Aminoalkyläthern von Alkoholen der aromatischaliphatischen Reihe | |
| CH446310A (de) | Verfahren zur Herstellung von Dibenzo-cyclohepten-Derivaten | |
| DE852991C (de) | Verfahren zur Herstellung organischer sauerstoffhaltiger Verbindungen | |
| AT335436B (de) | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, deren estern, amiden und salzen | |
| AT333735B (de) | Verfahren zur herstellung von neuen carbonsaureestern von 3-(4-biphenylyl)-1-butanolen und 3-(4-biphenylyl)-2-buten-1-olen | |
| AT270609B (de) | Verfahren zur Herstellung von 5-(3'-Methylaminopropyl)-5H-dibenzocycloheptaenverbindungen und ihren Säureadditionssalzen | |
| DE3118656A1 (de) | Verfahren zur herstellung von (alpha),ss-ungesaettigten aldehyden und 2,7-dimethyl-2,6-octadienal | |
| DE1470133C (de) | Substituierte alpha Pyrazinyl succinimide und Verfahren zu ihrer Herstellung | |
| AT262268B (de) | Verfahren zur Herstellung von neuen 1-Phenyl-2-alkylcyclohexanolen | |
| AT155800B (de) | Verfahren zur Herstellung von Diaminoalkoholen. | |
| AT336004B (de) | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, ihrer ester, amide und salze | |
| AT247850B (de) | Verfahren zur Herstellung von Dibenzocycloheptenverbindungen | |
| DE817595C (de) | Verfahren zur Herstellung alkylierter Azulene | |
| AT281825B (de) | Verfahren zur herstellung neuer zimtsaeureamide |